Hz, 2H), 6.08 (s, 1H), 3.81 (s, 3H), 2.93 (t, J = 7.1 Hz, 4H), 2.49 (s, 3H), 1.43 – 1.30 (m, 4H), 1.32
– 1.17 (m, 4H), 0.74 (t, J = 7.2 Hz, 6H).
5.1.1.7.4.
(E)-3-(3-(2-((E)-4-cyanobenzylidene)hydrazine-1-carboxamido)-4-(
dibutylamino)phenyl) but-2-enoic acid (7d)
White solid; Yield: 68.1%; Mp: 224-225 °C; MS (ESI) m/z (%): 474.7 [M-H]-. 1H NMR (400
MHz, DMSO-d6) δ(ppm): 12.16 (s, 1H), 11.30 (s, 1H), 9.64 (s, 1H), 8.44 (d, J = 2.1 Hz, 1H), 8.06
(s, 1H), 7.95 (d, J = 8.3 Hz, 2H), 7.87 (d, J = 8.4 Hz, 1H), 7.34 (d, J = 8.4 Hz, 1H), 7.23 (d, J = 8.3
Hz, 2H), 6.09 (s, 1H), 2.94 (t, J = 7.2 Hz, 4H), 2.49 (s, 3H), 1.35 (m, 4H), 1.29 – 1.15 (m, 4H),
0.72 (t, J = 7.2 Hz, 6H).
5.1.1.7.5. (E)-3-(3-(2-((E)-2,4-difluorobenzylidene)hydrazine-1-carboxamido)-4-(dibutylamino)
phenyl)but-2-enoic acid (7e)
1
Brown solid; Yield: 77.8%; Mp: 214-215 °C; MS (ESI) m/z (%): 485.5 [M-H]-. H NMR
(400 MHz, DMSO-d6) δ(ppm): 12.19 (s, 1H), 11.14 (s, 1H), 9.57 (s, 1H), 8.44 (s, 1H), 8.15 (s,
1H), 7.91 (q, J = 8.5, 7.8 Hz, 1H), 7.44 – 7.35 (m, 1H), 7.33 (d, J = 8.4 Hz, 1H), 7.29 – 7.19 (m,
2H), 6.08 (s, 1H), 2.96 – 2.88 (m, 4H), 2.49 (s, 3H), 1.34 (m, 4H), 1.28 – 1.17 (m, 4H), 0.72 (t, J =
7.2 Hz, 6H).
5.1.1.7.6.
(E)-3-(4-(dibutylamino)-3-(2-((E)-4-methylbenzylidene)hydrazine-1-carboxamido)
phenyl)but-2-enoic acid (7f)
White solid; Yield: 72.5%; Mp: 205-207 °C; MS (ESI) m/z (%): 463.4 [M-H]-. 1H NMR (400
MHz, DMSO-d6) δ 1H NMR (400 MHz, DMSO-d6) δ 12.18 (s, 1H), 10.89 (s, 1H), 9.57 (s, 1H),
8.45 (s, 1H), 7.96 (s, 1H), 7.60 (d, J = 8.1 Hz, 2H), 7.32 (d, J = 8.4 Hz, 1H), 7.29 – 7.17 (m, 3H),
6.08 (s, 1H), 2.99 – 2.81 (m, 4H), 2.49 (s, 3H), 2.34 (s, 3H), 1.43 – 1.30 (m, 4H), 1.31 – 1.16 (m,
4H), 0.74 (t, J = 7.3 Hz, 6H).
5.1.1.7.7.
(E)-3-(3-(2-((E)-4-chlorobenzylidene)hydrazine-1-carboxamido)-4-(dibutylamino)
phenyl)but-2-enoic acid (7g)
White solid; Yield: 76.8%; Mp: 215-218 °C; MS (ESI) m/z (%): 483.3 [M-H]-. 1H NMR (400
MHz, DMSO-d6)δ (ppm):12.20 (s, 1H), 11.06 (s, 1H), 9.60 (s, 1H), 8.44 (s, 1H), 8.00 (s, 1H), 7.72
(d, J = 8.5 Hz, 2H), 7.53 (d, J = 8.4 Hz, 2H), 7.33 (d, J = 8.3 Hz, 1H), 7.22 (d, J = 8.3 Hz, 1H),
6.09 (s, 1H), 2.93 (t, J = 7.1 Hz, 4H), 2.49 (s, 3H), 1.45 – 1.30 (m, 4H), 1.29 – 1.10 (m, 4H), 0.72
(t, J = 7.2 Hz, 6H). 13C NMR (100 MHz, DMSO-d6) δ 167.98 , 154.18 , 152.90 , 141.23 , 139.97 ,
138.39 , 136.49 , 134.47, 133.70 , 129.27 , 128.43 , 123.71 , 120.54 , 117.22 , 115.12 , 54.82 ,
29.81 , 20.28 , 17.57 , 14.20 .
5.1.1.7.8.
(E)-3-(4-(dibutylamino)-3-(2-((E)-4-(trifluoromethyl)benzylidene)hydrazine-1-
carboxamido)phenyl)but-2-enoic acid (7h)
1
Yellow solid; Yield: 69.8%; Mp: 213-215 °C; MS (ESI) m/z (%): 517.3 [M-H]-. H NMR
(600 MHz, DMSO-d6) δ 11.32 (s, 1H), 9.67 (s, 1H), 8.43 (d, J = 2.2 Hz, 1H), 8.15 (s, 1H), 7.91 (d,
J = 8.2 Hz, 2H), 7.82 (d, J = 8.2 Hz, 2H), 7.27 (d, J = 8.3 Hz, 1H), 7.15 (dd, J = 8.2, 2.2 Hz, 1H),
6.15 (s, 1H), 2.92 (t, J = 7.3 Hz, 4H), 2.45 (s, 3H), 1.34 (ddd, J = 12.1, 8.7, 6.2 Hz, 4H), 1.23 (h, J
= 7.3 Hz, 4H), 0.70 (t, J = 7.3 Hz, 6H).
5.1.1.7.9.
(E)-3-(4-(dibutylamino)-3-(2-((E)-2-(trifluoromethyl)benzylidene)hydrazine-1-
carboxamido)phenyl)but-2-enoic acid (7i)
1
Light yellow solid; Yield: 66.6%; Mp: 204-205 °C; MS (ESI) m/z (%): 519.4 [M+H]+. H
NMR (400 MHz, DMSO-d6) δ(ppm):12.15 (s, 1H), 11.30 (s, 1H), 9.61 (s, 1H), 8.44 (s, 1H), 8.37
(s, 1H), 8.17 (d, J = 7.8 Hz, 1H), 7.85 – 7.73 (m, 2H), 7.64 (t, J = 7.7 Hz, 1H), 7.33 (d, J = 8.4 Hz,